US985559A - Process of preparing bismuth beta-naphtholate. - Google Patents
Process of preparing bismuth beta-naphtholate. Download PDFInfo
- Publication number
- US985559A US985559A US51757209A US1909517572A US985559A US 985559 A US985559 A US 985559A US 51757209 A US51757209 A US 51757209A US 1909517572 A US1909517572 A US 1909517572A US 985559 A US985559 A US 985559A
- Authority
- US
- United States
- Prior art keywords
- beta
- solution
- naphthol
- bismuth
- naphtholate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title description 10
- GQMVAUFIUVHMBB-UHFFFAOYSA-K trinaphthalen-2-yloxybismuthane Chemical compound C1=CC=CC2=CC(O[Bi](OC=3C=C4C=CC=CC4=CC=3)OC=3C=C4C=CC=CC4=CC=3)=CC=C21 GQMVAUFIUVHMBB-UHFFFAOYSA-K 0.000 title 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229950011260 betanaphthol Drugs 0.000 description 9
- 229910052797 bismuth Inorganic materials 0.000 description 8
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 5
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 230000002421 anti-septic effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- CJJMLLCUQDSZIZ-UHFFFAOYSA-N oxobismuth Chemical compound [Bi]=O CJJMLLCUQDSZIZ-UHFFFAOYSA-N 0.000 description 2
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960002069 diamorphine Drugs 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
Definitions
- pound for internal use which shall consist As illustrating the distinctive characterof beta-naphthol in combination with bisistics of the product prepared by our procl5 Inuth oXid and shall not possess the objecess, if a given weight of said product be tionable taste and corrosive qualities charextracted with chloroform, evaporated care- 7 v acterizing beta-naphthol.
- the process of preparing the herein 45 employ, for example, twenty-five pounds of described compound of bismuth and betabeta-naphthol dissovled in a solution of naphthol which consists in dissolving betatwenty-eight pounds of sodium hydroxid in naphthol in a solution of sodium hytwenty gallons of water.
- naphthol which consists in dissolving betatwenty-eight pounds of sodium hydroxid in naphthol in a solution of sodium hytwenty gallons of water.
- droxid and water adding to said solufirst, a solution of 84 pounds of bismuth tion a second solution of bismuth nitrate 50 nitrate in a mixture of one hundred pounds and a mixture of acetic acid and water;
- glacial acetic acid and eleven gallons of then adding a further amount of sodium water, and then gradually add a solution of hydroxid; boiling the combined solutions; sixty-two pounds of sodium hydroxid in and separating the precipitate formed.
- TILLIAM E. BRADLEY VM. A. BARR.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
rich
JOSEPH L. TURNER, OF PHILADELPHIA, PENNSYLVANIA, AND CHARLES E. VANDER- KLEED, OF COLLINGSWOOD, NEW JERSEY, ASSIGNORS T H. K. MULFORD COMPANY, OF PHILADELPHIA, PENNSYLVANIA, A CORPORATION OF PENNSYLVANIA.
PROCESS OF PREPARING BISlVIUTI-I BETA-NAPHTHOLATE.
985,559. Specification of Letters Patent Patented Feb. 28, 1911.
No Drawing. Application filed September 14, 1909. Serial No. 517,572.
To all whom it may concern: boiled for from eight to ten hours under 55 Be it known that we, JosEPH L. TURNER, a constant stirring. The precipitate is then subject of the Czar of Russia, and CHARLES left to settle, the supernatant liquid is de- E. VANDERKLEED, a citizen of the United canted and the precipitate is washed by States, residing, respectively, in Philadelfiltration until the washings cease to show phia, Pennsylvania, and Oollingswood, New an alkaline reaction. The precipitate is 60 Jersey, have invented certain Improvements finally dried at a moderate temperature. in Processes for Preparing Bismuth Beta- The product resulting from the above de- Naphtholate, of which the following is a scribed process is the desired compound of specification. bismuth and beta-naphthol, which is a valu- The object of our invention is to provide able intestinal antiseptic possessing the 65 a process for preparing an antiseptic comqualities above indicated. pound for internal use which shall consist As illustrating the distinctive characterof beta-naphthol in combination with bisistics of the product prepared by our procl5 Inuth oXid and shall not possess the objecess, if a given weight of said product be tionable taste and corrosive qualities charextracted with chloroform, evaporated care- 7 v acterizing beta-naphthol. fully to dryness in a weighed flask and the Another object of our invention is to proresidue weighed, it will be found that said duce an antiseptic containing about 75% of Pr yle ds only lO llt (16% Of SXtIaC- 20 bismuth oxid and about 23% of b taa htive. It will further be noted that the thol in true chemical combination; th product obtained in the above determina- 75 compound, o over b in o r ar d tion presents a crystalline appearance, is that it shall not contain any of the decomready sublimable, and has a melting point position products of the beta-naphthol. of about 122 C.
25 In carrying out our invention, we first We cla1m:-
convert the beta-naphthol into its sodium salt 1. The process of preparing the herein 80 by dissolving it in the theoretical amount of described compound of bismuth and betasodium hydroxid. We then add to this sonaphthol which consists in converting betalution a solution obtained by dissOlVing naphthol into one of its alkaline salts; acting crystals f bi th it t i acetic acid, on said compound with an acid solution of then neutralize the nitric acid freed from bismuth nitrate; neutralizing the resulting 85 the bismuth nitrate and also the acetic acid, Solution; boiling said solution; and separatby a further addition of sodium hydroxid ing therefrom the compound of bismuth solution. The precipitate obtained by this and beta-naphthol.
process is a brownish gray powder contain- 2. The process of preparing the herein ing about 23% of beta-naphthol in combinadescribed compound of bismuth and beta- 9 tion with bismuth oXid, the reactions naphthol which consists in acting on betawhich occur in its formation being as folnaphthol with a solution of sodium hylows: droxid;badding 1thereto the solution ob- 40 tained disso vin bismuth nitrate in CH7fOH+NaOH:C1H7'ONa+H2O acetic acitl; neutralizing the resulting soluaigjggg OH +6NaN03 +1120 tion; boilingsaid solution; and separating V the precipitate formed. In actually carrying out the process, we 3. The process of preparing the herein 45 employ, for example, twenty-five pounds of described compound of bismuth and betabeta-naphthol dissovled in a solution of naphthol which consists in dissolving betatwenty-eight pounds of sodium hydroxid in naphthol in a solution of sodium hytwenty gallons of water. To this we add, droxid and water; adding to said solufirst, a solution of 84 pounds of bismuth tion a second solution of bismuth nitrate 50 nitrate in a mixture of one hundred pounds and a mixture of acetic acid and water;
glacial acetic acid and eleven gallons of then adding a further amount of sodium water, and then gradually add a solution of hydroxid; boiling the combined solutions; sixty-two pounds of sodium hydroxid in and separating the precipitate formed.
ten gallons of water, the whole being then 4. The process of preparing the heroin described compound of bismuth and beta- -naphthol which consists in dissolving 25 pounds of beta-naphthol in a solution of 28 pounds of sodiunrhydroxid in 20 gallons of Water; adding to the same, first a solution of Set pounds of bismuth nitrate and 100 pounds of glacial acetic acid in 11 gallons of Water, and then a solution of 62 pounds of sodium hydroXid in 10 gallons of Water;
10 boiling the solutions and separating out the 1 resulting precipitate; the proportions of the ingredients being substantially as specified. In testimony whereof, W6 have signed our names to this specification in the presence of two subscribing Witnesses.
JOSEPH L. TURNER. CHARLES E. VANDERKLEED. \Vitnesses:
TILLIAM E. BRADLEY, VM. A. BARR.
Copies of this patent may be obtained for five cents each, by addressing the Commissioner of Patents,
Washington, D. G.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51757209A US985559A (en) | 1909-09-14 | 1909-09-14 | Process of preparing bismuth beta-naphtholate. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51757209A US985559A (en) | 1909-09-14 | 1909-09-14 | Process of preparing bismuth beta-naphtholate. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US985559A true US985559A (en) | 1911-02-28 |
Family
ID=3053903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US51757209A Expired - Lifetime US985559A (en) | 1909-09-14 | 1909-09-14 | Process of preparing bismuth beta-naphtholate. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US985559A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3223720A (en) * | 1962-06-18 | 1965-12-14 | Angeli Inst Spa | Aluminum pamoate |
-
1909
- 1909-09-14 US US51757209A patent/US985559A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3223720A (en) * | 1962-06-18 | 1965-12-14 | Angeli Inst Spa | Aluminum pamoate |
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